Triacetoxyperiodinane → tert-Butyl 4-(3-chloro-2-oxopropyl)-3-oxopiperazine-1-carboxylate

HRID 335250Notes

Reaction equation

HRID 335250 reaction equation
[Cl:1][CH2:2][CH:3]([OH:19])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][C:6]1=[O:18].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(#N)C.C(OCC)(=O)C>[Cl:1][CH2:2][C:3](=[O:19])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH2:7][C:6]1=[O:18]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66995243Tert-butyl 4-(3-chloro-2-hydroxypropyl)-3-oxopiperazine-1-carboxylate

Product 1

HCID 86631533tert-Butyl 4-(3-chloro-2-oxopropyl)-3-oxopiperazine-1-carboxylateYield 18.31%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 125 ml round-bottom flask equipped with a magnetic stirrer tert-butyl 4-(3-chloro-2-hydroxypropyl)-3-oxopiperazine-1-carboxylate (3.30 g, 11.3 mmol) was dissolved in acetonitrile (10 ml) and Dess-Martin periodinane (5.26 g, 12.4 mmol) was added. After agitating for 3 hours the mixture was diluted with ethyl acetate (100 ml) and washed with sodium bicarbonate and brine, dried and evaporated. Purified by column chromatography and eluting with 3% MeOH/CH2Cl2 to give the title compound (0.600 g, 18.31% yield).

Workup

  1. washwashed with sodium bicarbonate and brine
  2. customdried
  3. customevaporated
  4. customPurified by column chromatography
  5. washeluting with 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-0a4e08aec14b4ab6a41253a366cea821
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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